Synthetic studies on nemorosone via enantioselective intramolecular cyclopropanation
Synthetic studies on nemorosone via enantioselective intramolecular cyclopropanation
复制标题
DOI：
10.1016/j.tetlet.2009.12.147
复制
发表时间：
2010-03-03
影响因子：
1.8
通讯作者：
Nakada, Masahisa
中科院分区：
文献类型：
--
作者：
Abe, Masahito;Saito, Aya;Nakada, Masahisa
本文介绍了通过对映体选择性分子内环丙烷化合成尼莫司酮的研究。通过分子内环丙化、环丙烷二甲基化和烷基化环丙烷的开环反应，对三种可能的中间体的合成效率进行了评价。结果表明，α-重氮甲基酮10c是最合适的。本文还介绍了用对映选择性分子内环丙烷化反应来构建双环[3，3，1]正庚烷核，并制备了具有所有正确的尼莫酮立体生成中心的化合物。(C)2010爱思唯尔有限公司保留所有权利。
This Letter describes synthetic studies of nemorosone via enantioselective intramolecular cyclopropanation. For the total synthesis of nemorosone, three potential intermediates were evaluated through the efficiency of three sequential reactions, namely, their intramolecular cyclopropanation, dimethylation of the resultant cycloproparies, and ring-opening reaction of the alkylated cyclopropanes. As a result, alpha-diazomethyl ketone 10c was found to be the most suitable. The enantroselective intramolecular cyclopropanation to construct the bicyclo[3 3 1]nonane core and preparation of the compound with all the correct stereogenic centers of nemorosone are also described. (C) 2010 Elsevier Ltd All rights reserved.